Record Information
Version1.0
Creation date2010-04-08 22:09:54 UTC
Update date2018-05-28 23:32:36 UTC
Primary IDFDB011930
Secondary Accession Numbers
  • FDB030818
Chemical Information
FooDB Name2,3-Butanedione
DescriptionConstituent of butter; formed during fermentation. A common constituent of plant oils, production of breakdown of carbohydrates. Flavouring additive used in food industryand is also present in apple, orange, plum, okra, walnut, Bourbon vanilla, clary sage, soybean, coffee, honey, rose wine, port wine, cocoa and scallop Beer sometimes undergoes a diacetyl rest, in which its temperature is raised slightly for two or three days after fermentation is complete, to allow the yeast to absorb the diacetyl it produced earlier in the fermentation cycle. The makers of some wines, such as chardonnay, deliberately promote the production of diacetyl because of the feel and flavor it imparts. It is present in many California chardonnays known as "Butter Bombs," although there is a growing trend back toward the more traditional French styles.[citation needed]; Diacetyl (IUPAC systematic name: butanedione or 2,3-butanedione) is a natural byproduct of fermentation. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2. Diacetyl occurs naturally in alcoholic beverages and is added to some foods to impart a buttery flavor.; Diacetyl is a natural by-product of secondary or malolactic fermentation. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2.; Carrier of aroma of butter, vinegar, coffee, and other foods.; Beer sometimes undergoes a diacetyl rest, which entails waiting two or three days after fermentation is complete, to allow the yeast to absorb the diacetyl it produced earlier in the fermentation cycle. The makers of some wines, such as chardonnay, deliberately promote the production of diacetyl because of the feel and flavors it imparts. 2,3-Butanedione is found in many foods, some of which are capers, linden, sweet marjoram, and brazil nut.
CAS Number431-03-8
Structure
Thumb
Synonyms
SynonymSource
2,3-ButadioneChEBI
2,3-ButandioneChEBI
2,3-ButanedioneChEBI
2,3-DiketobutaneChEBI
2,3-DioxobutaneChEBI
BiacetylChEBI
Dimethyl glyoxalChEBI
DimethylglyoxalChEBI
AcetoacetaldehydeHMDB
ButadioneHMDB
Butan-2,3-dioneHMDB
Butane-2,3-dioneHMDB
ButanedioneHMDB
Dimethyl diketoneHMDB
DimethyldiketoneHMDB
DiketobutaneHMDB
2,3 ButanedioneHMDB
(CH3CO)2biospider
2,3 Butandione (Diacetyl)biospider
2,3-Butanedione (8CI,9CI)biospider
2,3-butanedione (diacetal)biospider
2,3-Butanedione (Diacetyl)biospider
2,3-butanodionebiospider
buta-2,3-dionebiospider
Butan-2,3-dione (diacetyl)biospider
Butanal, 3-oxo-biospider
Butane-2,3-dione (diacetyl)biospider
Butanedione (diacetyl)biospider
Butanedione [UN2346]biospider
Butanedione [UN2346] [Flammable liquid]biospider
Diacetyldb_source
Dotriacontanebiospider
FEMA 2370db_source
Glyoxal, dimethyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility129 g/LALOGPS
logP0.07ALOGPS
logP0.4ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)15.98ChemAxon
pKa (Strongest Basic)-8.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.54 m³·mol⁻¹ChemAxon
Polarizability8.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H6O2
IUPAC namebutane-2,3-dione
InChI IdentifierInChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
InChI KeyQSJXEFYPDANLFS-UHFFFAOYSA-N
Isomeric SMILESCC(=O)C(C)=O
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
Classification
Description belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-diketones
Alternative Parents
Substituents
  • Alpha-diketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Industrial process:

Role

Industrial application:

Environmental role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.81%; H 7.02%; O 37.17%DFC
Melting PointFp 7°DFC
Boiling PointBp 88°DFC
Experimental Water Solubility200 mg/mL at 15 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP-1.34HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.94DFC
Refractive Indexn18.5D 1.3933DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-eeaaf8aa838a1d6a7ddeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-622030119adee3079d84View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-eeaaf8aa838a1d6a7ddeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-622030119adee3079d84View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-58f4b3973bdf0094a5e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-4e7132ef8eb6971544b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00r5-9000000000-0cc5c90a4394d550268fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-06dj-9000000000-a74bfecfcdb93a5c3e07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-eeaaf8aa838a1d6a7ddeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-171c3774c90fd50b6d6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-e8c63126caa0f371f336View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-82affa84acc0579c193bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f63598734c0af05eb392View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-e8c63126caa0f371f336View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-82affa84acc0579c193bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f63598734c0af05eb392View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2599bbcd002f75cefa1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-1171c0cf98959e7315c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-7dcc0fc66bb1e551b332View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2599bbcd002f75cefa1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-1171c0cf98959e7315c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-7dcc0fc66bb1e551b332View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-8d1a3988261033033e03View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID630
ChEMBL IDCHEMBL365809
KEGG Compound IDC00741
Pubchem Compound ID650
Pubchem Substance IDNot Available
ChEBI ID16583
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03407
CRC / DFC (Dictionary of Food Compounds) IDHBW35-X:HBW35-X
EAFUS ID871
Dr. Duke IDBUTANEDIONE|BIACETYL|DIACETYL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID431-03-8
GoodScent IDrw1014611
SuperScent ID650
Wikipedia IDDiacetyl
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
irritantDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
butter
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
strong
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
creamy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).